The macquarimicins and cochleamycins are two recently isolated classes of novel natural products which have shown good antitumor activity against P388 leukemia cells. This proposal outlines a unified synthetic strategy for the construction of all members of these two families in an asymmetric fashion with a particular focus on the most potent member: macquarimicin B. The key step in the proposal is the novel merger of two separate technologies, the Claisen rearrangement and the hydroxyl- directed ketone reduction, into a one-pot conversion of a beta-hydroxy- allyl-enol ether into a syn-1,3-diol.